Synthesis of isocoumarins and α-pyrones via tandem Stille reaction/heterocyclization

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6669-6675

  Cherry, Khalil ^a   Parrain, Jean Luc ^b   Thibonnet, Jérôme ^a,b   Buchêne, Alain ^a   Abarbri, Mohamed ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; PALLADIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ISOCOUMARINS; OXYACYCLIZATION; PALLADIUM ACETATE; STILLE REACTION;

AROMATIC COMPOUNDS;

2 IODOBENZOIC ACID; 2 PYRONE DERIVATIVE; AROMATIC COMPOUND; IODOVINYLIC ACID DERIVATIVE; ISOCOUMARIN DERIVATIVE; N,N DIMETHYLFORMAMIDE; PALLADIUM ACETATE; TETRABUTYLAMMONIUM; TRIBUTYLTIN; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; HETEROCYCLIZATION; PRODUCT RECOVERY; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TANDEM STILLE REACTION;

CYCLIZATION; ISOCOUMARINS; MAGNETIC RESONANCE SPECTROSCOPY; PYRONES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 23644451647     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050638z     Document Type: Article

References (116)

1. (a) Barry, R. D. Chem. Rev. 1964, 229.
2. (b) Dickinson, J. Nat. Prod. Rep. 1993, 10, 71.
3. (c) Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493.
4. (d) Sugimoto, A.; Shinba-Tanaka, H.; Ishikawa, M. Synthesis 1995, 431.
5. (e) Goff, D. A.; Zuckermann, R. N. J. Org. Chem. 1995, 60, 5748.
6. (a) Chen, C.-H.; Liao, C.-C. Org. Lett. 2000, 2, 2049.
7. (b) Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690.
8. (c) Danieli, B.; Lesma, G.; Martinelli, M.; Passarella, D.; Peretto, I.; Silvani, A. Tetrahedron 1998, 54, 14081.
9. (d) Jram, V.; Goel, A. J. Chem. Res., Synop. 1997, 460.
10. (e) Liu, Z.; Meinwald, J. J. Org. Chem. 1996, 61, 6693.
11. (f) Afarinkia, K.; Berna-Canovas, J. Tetrahedron Lett. 2000, 41, 4955.
12. (g) Stigers, K. D.; Mar-Tang, R.; Bartlett, P. A. J. Org. Chem. 1999, 64, 8409.
13. (h) Cobas, A.; Diaz, M. T.; Escudero, S.; Pérez, D.; Guitiàn, E.; Castedo, L. In Current Trends in Organic Synthesis; Scolastico, C., Nicotra, F., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; pp 307-314.
14. (i) Ram, V. J.; Srivastava, P.; Saxena, A. S. J. Org. Chem. 2001, 66, 5333.
15. (a) Livingstone, R. In Rodd's Chemistry of carbon compounds; Caffey, S., Ed.; Elsevier: New York, 1977; vol. IV, Part E, pp 290-297.
16. (b) Hill, R. A. Progress in the Chemistry of Organic Natural Products; Springer-Verlag: Weinheim-New York, 1986; Vol. 49, pp 1-78.
17. (a) Naser-Hijazi, B.; Stolze, B.; Zanker, K. S. Second Proceedings of the International Society of the Coumarin Investigators; Springer: Berlin, 1994.
18. (b) Murray, R. D. H.; Méndez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry; J. Wiley: New York, 1982.
19. (a) Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 1999, 7, 1445.
20. (b) Yoshikawa, M.; Harada, E.; Naitoh, Y.; Inoue, K.; Matsuda, H.; Shimoda, H.; Yamahara, J.; Murakami, N. Chem. Pharra. Bull. 1994, 42, 2225.
21. (a) Matsuda, H.; Shimoda, H.; Yamahara, J.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 1998, 8, 215.
22. (b) Shimoda, H.; Matsuda, H.; Yamahara, J.; Yoshikawa, M. Biol. Pharm. Bull. 1988, 21, 809.
23. Whyte, A. C.; Gloer, J. B.; Scott, J. A.; Mallock, D. J. Nat. Prod. 1996, 59, 765.
24. Nozawa, K.; Yamada, M.; Tsuda, Y.; Kawai, K.; Nakajima, S. Chem. Pharm. Bull. 1981, 29, 2689.
25. Furuta, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 1986, 25, 517.
26. (a) Khalmuradov, M. A.; Said-Khodzhaev, A. I. Chem. Nat. Compd. 1999, 35, 364.
27. (b) Murakami, A.; Gao, G.; Omura, M.; Yano, M.; Ito, C.; Furukawa, H.; Takahashi, D.; Koshimizu, K.; Ohigashi, H. Bioorg. Med. Chem. Lett. 2000, 10, 59.
28. (c) Maier, W.; Schmidt, J.; Nimtz, M.; Wray, V.; Strack, D. Phytochemistry 2000, 54, 473.
29. (d) Garcia-Argaez, A. N.; Ramirez-Apan, T. O.; Delgado, H. P.; Velazquez, G.; Martinez-Vazquez, M. Planta Med. 2000, 66, 279.
30. (e) Wu, J.; Wang, L.; Fathi, R.; Yang, Z. Tetrahedron Lett. 2002, 43, 4395.
31. (a) Mishra, A.; Dash, B. L.; Behera, R. K. Ind. J. Heterocycle. Chem. 1996, 6, 149.
32. (b) Nicolaides, D. N.; Fylaktakidou, K.; Litinas, E. K.; Papageorgiou, G.; Hadjipavlou-Litina, D. J. J. Heterocycle. Chem. 1998, 35, 619.
33. (c) Fall, Y.; Teran, C.; Teijeira, M.; Santana, L.; Uriarte, E. Synthesis 2000, 643.
34. (d) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274.
35. (e) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. J. Org. Chem. 1995, 60, 3270.
36. (f) Izumi, T.; Morishita, N. J. Heteroycl. Chem. 1994, 31, 145.
37. (g) Ohta, S.; Kamata, Y.; Inagaki, T.; Masuda, Y.; Yamamoto, S.; Yamashita, M.; Kawasaki, I. Chem. Pharm. Bull. 1993, 41, 1188.
38. (h) Yoshikawa, M.; Harada, E.; Yagi, N.; Okuno, Y.; Muraoka, O.; Aoyama, H.; Murakami, N. Chem. Pharm. Bull. 1994, 42, 721.
39. (i) Yoshikawa, M.; Shimada, H.; Yagi, N.; Murakami, N.; Shimoda, H.; Yamahara, J.; Matsuda, H. Chem. Pharm. Bull. 1996, 44, 1890.
40. (j) Mali, R. S.; Babu, K. N. J. Org. Chem. 1988, 53, 4676.
41. (k) Rama, N. H.; Iqbal, R.; Zamani, K.; Saeed, A.; Iqbaql, M. Z.; Choudhary, M. I. Indian J. Chem., Sect. B 1998, 37, 365.
42. (l) Bovicelli, P.; Lupattelli, P.; Crescenzi, B.; Sanetti, A.; Bernini, R. Tetrahedron 1999, 55, 14719.
43. (m) Mal, D.; Bandyopadhyay, M.; Ghorai, S. K.; Datta, K. Tetrahedron Lett. 2000, 41, 3677.
44. (n) Hussain, M. T.; Rama, N. H.; Malik, A. Indian J. Chem., Sect. B 2001, 40, 372.
45. (o) Natsugari, H.; Ikeura, Y.; Kiyota, Y.; Ishichi, Y.; Ishimaru, T.; Saga, O.; Shirafuji, H.; Tanaka, T.; Kamo, T.; Doi, T.; Otsuka, M. J. Med. Chem. 1995, 38, 3106.
46. (p) Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron 2003, 59, 2067.
47. (q) An, Z.; Catellani, M.; Chiusoli, G. P. Gazz. Chim. Ital. 1990, 120, 383.
48. (r) Catellani, M.; Chiusoli, G. P.; Solari, G. Tetrahedron Lett. 1994, 35, 5919.
49. (s) Catellani, M.; Chiusoli, G. P.; Fagnola, M. C.; Solari, G. Tetrahedron Lett. 1994, 35, 5923.
50. (t) Johnson, J. R. Org. React. 1942, 1, 210.
51. (u) Sethna, S.; Phadke, R. Org. React. 1953, 7, 1.
52. (a) Vara Prasad, J. V. N.; Para, K. S.; Lunney, E. A.; Ortwine, D. F.; Dunbar, J. B., Jr.; Fergunson, D. Tummino, P. J.; Hupe, D.; Tait, B. D.; Domagala, J. M.; Humblet, C. Bhat, T. N.; Liu, B.; Guerin, D. A. M.; Baldwin, E. T.; Erickson, J. W.; Sawyer, T. K. J. Am. Chem. Soc. 1994, 116, 6989.
53. (b) Tuanli, Y.; Larock, R. C. J. Org. Chem. 2003, 68, 5936.
54. (a) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Heterocycles 1995, 41, 2587.
55. (b) Bellina, F.; Ciucci, D.; Vergamini, P.; Rossi, R. Tetrahedron 2000, 56, 2533.
56. (c) Rossi, R.; Bellina, F.; Biagetti, M.; Catanese, A.; Mannina, L. Tetrahedron Lett. 2000, 41, 5281.
57. (d) Minami, T.; Nishimoto, A.; Nakamura, M. Chem. Pharm. Bull. 1994, 42, 170.
58. (e) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett. 2001, 42, 2852.
59. (f) Kvita, V.; Fischer, W. Chimica 1992, 45, 457.
60. (g) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2003, 68, 9423.
61. For a recent synthesis using Pd or Ag catalysts, see: (a) Xu, C.; Negishi, E. Tetrahedron Lett. 1999, 40, 431.
62. (b) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387.
63. (c) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799.
64. (d) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599.
65. (e) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017.
66. (f) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135.
67. (g) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
68. (h) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796.
69. (i) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1996, 61, 3238.
70. (j) Ogawa, Y.; Maruno, M.; Wakamatsu, T. Synlett 1995, 871.
71. Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770.
72. Anastasia, L.; Xu, C.; Negishi, E. Tetrahedron Lett. 2002, 43, 5673.
73. (a) Duchêne, A.; Abarbri, M.; Parrain, J.-L.; Kitamura, M.; Noyori, R. Synlett 1994, 524.
74. (b) Abarbri, M.; Parrain, J.-L.; Cintrat, J. C.; Duchêne, A. Synthesis 1996, 82.
75. Rousset, S.; Abarbri, M.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L. Org. Lett. 1999, 1, 701.
76. Rousset, S.; Abarbri, M.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L. Chem. Commun. 2000, 1987.
77. (a) Tanaka, H.; Hai, A. K.; Ogawa, A. H.; Torii, S. Synlett 1993, 835.
78. (b) Brandsma, L. Synthesis of Acetylenes, Allenes, and Cumulenes: a laboratory manual; Elsevier Scientific Pub. Co.: New York, 1981.
79. Rousset, S.; Abarbri, M.; Thibonnet, J.; Parrain, J.-L.; Duchêne, A. Tetrahedron Lett. 2003, 44, 7633.
80. Larock, R. C.; He, Y.; Leon, W. W.; Han, X.; Refvik, M. D.; Zenner, M. J. J. Org. Chem. 1998, 63, 2154.
81. Yamamoto, Y.; Al-Masum, M.; Fujiwara, N. J. Chem. Soc., Chem. Commun. 1996, 381.
82. (a) Izumi, T.; Nishimoto, Y.; Kohei, K.; Kasahara, A. J. Heterocycle. Chem. 1990, 27, 1419.
83. (b) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1988, 27, 453.
84. Sakamoto, T.; Kondo, Y.; Yasuhara, A.; Yamanaka, H. Tetrahedron 1991, 47, 1877.
85. (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1988, 27, 2225.
86. (b) Sakamoto, T.; An-naka, M.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2754.
87. Sakamoto, T.; An-naka, M.; Kondo, Y.; Araki, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1890.
88. Korte, D. E.; Hegedus, L. S.; Wirth, R. K. J. Org. Chem. 1977, 42, 1329.
89. Wang, L.; Shen, W. Tetrahedron Lett. 1998, 39, 7625.
90. Kadnikov, D. V.; Larock, R. C. J. Organomet. Chem. 2003, 687, 425.
91. Kundu, N. G.; Pal, M.; Nandi, B. J. Chem. Soc., Perkin Trans. 1 1998, 561.
92. Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun. 1993, 86.
93. (a) Liao, H.-Y.; Cheng, C.-H. J. Org. Chem. 1995, 60, 3711.
94. (b) Sashida, H.; Kawamukai, A. Synthesis 1999, 1145.
95. (a) Meyers, A. I.; Temple, D. L.; Haidukewych, D.; Mihelich, E. D. J. Org. Chem. 1974, 39, 2787.
96. (b) Meyers, A. I.; Mihelich, E. D. J. Org. Chem. 1975, 40, 3158.
97. (c) Liang, P.-H.; Hsin, L.-W.; Pong, S.-L.; Hsu, C.-H.; Cheng, C.-Y. J. Chin. Chem. Soc. 2003, 50, 449.
98. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
99. (b) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
100. (c) Mitchell, T. N. Synthesis 1992, 803.
101. (d) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 12, Chapter 3.4, pp 161-241.
102. (e) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: New York, 1996; Vol. 5, pp 1-53.
103. (f) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Org. React.; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 50, Chapter 1, pp 1-652.
104. (g) Farina, V.; Krishnamurthy, V. The Stille Reaction; Wiley: New York, 1999.
105. (a) Kotretsou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161.
106. (b) Izumi, T.; Kasahara, A. Bull. Chem. Soc. Jpn. 1975, 48, 1673.
107. (a) Zhou, M.; Yoshida, Y.; Ishii, S.; Noguchi, H. Synth. Commun. 1999, 29, 2241.
108. (b) Dieter, R. K.; Fishpaugh, J. R. J. Org. Chem. 1988, 53, 2031.
109. (a) Kalinin, V. N.; Shilova, O. S.; Okladnoi, D. S.; Schmidhammer, H. Dokl. Akad. Nauk 1996, 351, 67.
110. (b) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F. J.; Schmidt, J. P. Bioorg. Med. Chem. 2004, 12, 4285.
111. Dieter, R. K.; Fishpaugh, J. R. J. Org. Chem. 1987, 52, 923.
112. Pittet, A. O.; Klaiber, E. M. J. Agric. Food Chem. 1975, 23, 1189.
113. (a) Sashida, H.; Kawamukai, A. Synthesis 1999, 1145.
114. (b) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274.
115. Tirodkar, R. B.; Vsgaonkar, R. N. Indian J. Chem. 1970, 8, 123.
116. Hauser, F. M.; Dorsch, W. A.; Mal, D. Org. Lett. 2002, 4, 2237.